Triamcinolone

Structural formula
General
Non-proprietary name	Triamcinolone
other names	11 β , 16 α , 17 α , 21-tetrahydroxy-9 α -fluoro-1,4-pregnadiene-3,20-diones; (8 S , 9 R , 10 S , 11 S , 13 S , 14 S , 16 R , 17 S ) -9-fluoro-11,16,17-trihydroxy-17- (2-hydroxyacetyl) -10,13- dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta [ a ] phenanthren-3-one ( IUPAC ) ; Fluoxyprednisolone;
Molecular formula	C 21 H 27 FO 6
External identifiers / databases
EC number	204-718-7
ECHA InfoCard	100.004.290
PubChem	31307
DrugBank	DB00620
Wikidata	Q1074056
Drug information
ATC code	A01 AC01 , C05 AA12 , D07 AB09 , H02 AB08 , R01 AD11 , R03 BA06 , S01 BA05
Drug class	Glucocorticoids
properties
Molar mass	394.4 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 351
	P: 281
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triamcinolone is a drug from the group of synthetic glucocorticoids . It has anti-allergic, anti-inflammatory and immunosuppressive effects . Triamcinolone is used for the systemic treatment of inflammatory rheumatic diseases, allergic, chronic inflammatory and chronic obstructive pulmonary diseases , severe forms of glucocorticoid-sensitive skin diseases and inflammatory kidney diseases. The triamcinolone derivatives triamcinolone acetonide and triamcinolone hexacetonide are also used therapeutically .

Clinical information

Application areas (indications)

Triamcinolone is approved in the form of tablets for the systemic treatment of a large number of allergic, inflammatory and immunological diseases.

In the Rheumatology this glucocorticoid is, inter alia, for the treatment of active phase of Systemvaskulitiden , such as polyarteritis nodosa , rheumatic system diseases such as systemic lupus erythematosus and mixed connective tissue disease , and rheumatoid arthritis used with severe progressive course shape. Further rheumatological areas of application are polymyalgia , reactive arthritis, arthritis in sarcoidosis and Still syndrome . In particularly severe forms and when non-steroidal anti-inflammatory drugs cannot be used, triamcinolone is also used to treat other rheumatic diseases such as spondarthritis. In rheumatology, the triamcinolone derivative triamcinolone hexacetonide is also used as an intra-articular suspension injection .

In pulmonology , triamcinolone is used for the long-term treatment of severe chronic bronchial asthma and for the short -term treatment of exacerbations in chronic obstructive pulmonary diseases and asthma exacerbations.

In the allergy oral triamcinolone is for short-term treatment of severe forms of allergic rhinitis used when other treatment options, including topical glucocorticoids such as betamethasone - ester attached and triamcinolone acetonide, no success.

In dermatology , oral triamcinolone is used for the initial treatment of acute relapses of severe, large-area skin diseases that respond to glucocorticoids, such as allergic dermatoses , atopic eczema and pemphigus vulgaris . The locally active triamcinolone derivative triamcinolone acetonide is used for external topical treatment. In addition, triamcinolone hexacetonide is used as a sub- and intralesional suspension injection in dermatology.

Areas of application in nephrology include the treatment of various forms of glomerulonephritis and the treatment of idiopathic retroperitoneal fibrosis .

Contraindications (contraindications)

If there is a known hypersensitivity to triamcinolone, treatment with this active ingredient is contraindicated . Triamcinolone may only be used systemically for acute viral infections, acute and chronic bacterial infections, systemic mycoses and parasitoses, poliomyelitis, lymphadenitis after BCG vaccination and a history of tuberculosis if the indications are strict. A strict risk-benefit assessment is also carried out when using live vaccines between 8 weeks before and 2 weeks after vaccinations . A strict indication is also necessary in the presence of gastric or duodenal ulcers , severe osteoporosis , difficult to control hypertension , difficult to control diabetes mellitus , psychiatric diseases, narrow and open angle glaucoma as well as corneal ulcerations and corneal injuries . Oral triamcinolone may only be used under strict supervision despite severe ulcerative colitis with the risk of perforation, diverticulitis and enteric anastomoses .

Drug interactions

Because of its multitude of effects, triamcinolone, like all other glucocorticoids, exhibits a broad spectrum of pharmacodynamic drug interactions . Because of common side effects, the risk of gastrointestinal bleeding is increased with simultaneous use with non-steroidal anti-inflammatory drugs. Since triamcinolone affects the body's mineral balance , the loss of potassium is increased by saluretics and laxatives . The effects and side effects of cardiac glycosides are exacerbated by the triamcinolone-related potassium deficiency. Due to its properties as a glucocorticoid on the carbohydrate metabolism, the blood sugar level -lowering effect of antidiabetic drugs is reduced.

Since triamcinolone via the cytochrome P450 - isoenzyme CYP3A4 is metabolized lead CYP3A4 inducers, such as phenytoin and carbamazepine , -nebenwirkungen to a reduction in Triamcinolonwirkungen and. In contrast, CYP3A4 inhibitors, such as the azole antimycotics ketoconazole and itraconazole , but also estrogens can lead to an intensification of the effect and side effects of triamcinolone. Antacids can decrease the oral bioavailability of triamcinolone.

Further interactions have been described with ephedrine , praziquantel , somatropin , ACE inhibitors , non-depolarizing muscle relaxants , antimalarials , protirelin , ciclosporin and coumarins .

Adverse effects (side effects)

As with all systemically administered glucocorticoids, there is a risk of developing Cushing's syndrome after long-term use of higher doses . Due to its mineralocorticoid side effects , triamcinolone can lead to sodium retention and increased potassium excretion. Taking triamcinolone can also affect cholesterol and triglyceride metabolism.

Possible side effects on skeletal muscles and connective tissue include muscle weakness and atrophy , osteoporosis , bone necrosis, and torn tendons . Adverse drug effects on the skin and subcutaneous tissue are atrophy , striae , steroid acne , delayed wound healing , changes in skin pigmentation, telangiectasia , instability of the capillary walls, petechiae , ecchymosis , hypertrichosis , rosacea-like dermatitis and hypersensitivity reactions. Furthermore, diseases of the nervous system, the gastrointestinal tract, the blood and lymphatic system, the immune system as well as eye diseases, vascular diseases and psychiatric diseases have been described as possible consequences of taking triamcinolone.

Pharmacological properties

Mechanism of action (pharmacodynamics)

Triamcinolone is a glucocorticoid and as such binds to the cytosolic glucocorticoid receptor . After the ligand - receptor complex activated in this way has been transported into the cell nucleus , glucocorticoid-dependent genes are transactivated with a glucocorticoid response element or transrepression , an inhibition of transcription by blocking other transcription factors . Due to an increased biosynthesis of anti-inflammatory proteins and an inhibition of the biosynthesis of pro-inflammatory proteins, this glucocorticoid has antiallergic, anti-inflammatory and immunosuppressive properties. As a glucocorticoid, triamcinolone also has effects on the carbohydrate, protein and fat metabolism.

Triamcinolone is about twice as potent as prednisone . Its moderate potency is increased by modifying the hydroxyl group in position 17, as in the case of triamcinolone acetonide. Compared to prednisolone, triamcinolone has a lower mineralocorticoid activity.

Absorption and distribution in the body (pharmacokinetics)

The plasma half-life of triamcinolone is 5 hours. Due to the gene induction and the gene repression as the principle of the glucocorticoid mode of action, the onset of action and the duration of action are time-shifted to the active substance plasma level. Metabolism in the liver occurs through conjugation with gluconic acid or through sulfation . Conjugated triamcinolone is mainly excreted in the urine .

Chemical and pharmaceutical information

Triamcinolone acetonide, a ketal of triamcinolone, is used in particular in the topical treatment of allergic and inflammatory diseases. Due to the modification of the hydroxyl group in position 17, triamcinolone acetonide has a higher potency than triamcinolone. Triamcinolone hexacetonide, which is also used therapeutically, is a lipophilic prodrug of triamcinolone acetonide.

Trade names

Monopreparations

Delphicort (A), Volon (D)

Individual evidence

↑ ^a ^b Triamcinolone data sheet from Sigma-Aldrich , accessed on May 25, 2017 ( PDF ).

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Technical information Volon 4/8/16 mg. Dermapharm AG. As of April 2011.

↑ Moore CD, Roberts JK, Orton CR, et al. : Metabolic Pathways of Inhaled Glucocorticoids by the Cyp3a Enzymes . In: Drug Metab. Dispos. . November 2012. doi : 10.1124 / dmd.112.046318 . PMID 23143891 .

[Sigma-1] Triamcinolone data sheet from Sigma-Aldrich , accessed on May 25, 2017 ( PDF ).

[FI_Volon-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Technical information Volon 4/8/16 mg. Dermapharm AG. As of April 2011.

[pmid23143891-3] Moore CD, Roberts JK, Orton CR, et al. : Metabolic Pathways of Inhaled Glucocorticoids by the Cyp3a Enzymes . In: Drug Metab. Dispos. . November 2012. doi : 10.1124 / dmd.112.046318 . PMID 23143891 .